The Rich Girl
by ourfuture
Summary: Alyssa Mongomery plays two roles, daughter of Frank Montgomery, the richest man in New York and friend to the Manhattan Newsies. She had a great life and was happy, until the strike came along. Now she has to choose between her family and friends, and when the King Of Brooklyn comes along, the decision will only get harder.
1. Prologue

Most people say a rich girl can't be friends with newsies, but for me that's a completely different story. I was best friends with the Manhattan newsies and had been for a while. But if my father ever found out I was friends with them, I would hate to see what would happen. In some way it was my father's fault I was friends with them. It was his fault I met Jack Kelly.

 _It was a cold winter's morning and a younger version of me was in my bedroom trying to find the warmest clothes possible, but that was quite difficult considering almost everything I owned was made out of thin cotton._

 _That day, I was going to meet my best friend Christina, so we could go for a walk around Central Park, like most people did at that time of year._

 _Once I'd finished getting ready, and was wearing a relatively warm pink, lacy dress, making sure I had a shawl with me, I proceeded to walk down my winding staircase and towards the front door. On the way out, I got stopped by me father, who gave me a questionable look._

 _"Where are you going, Alyssa?" questioned my father._

 _"To meet Christina at Central Park. We're going to go on a walk." I answered, smiling as sweetly as I could._

 _"I find it very good that you're getting fresh air, but please be careful, New York can be a terrifyng place." pleaded my father._

 _"I promise I'll be careful, father." I smiled._

 _"Very well, have fun. But while you're out, could you please get me a paper?" asked my father, while handing me a dollar._

 _"Of course, father." I said, as I clenched the dollar in my hand._

 _My father smiled at me, before I headed out into the vast city. It took my a while to fully take in my surroundings, but as soon as I did, all I could hear was the sound of newsies yelling from every street corner._

 _I proceeded down the street, where I saw quite a tall newsboy, giving a paper to a very nice old lady that lived near my friend Katherine. Deciding that this was the best newsboy, to go to, I reached up my hand and tapped him on the shoulder. Quickly, he turned around and gave a bright smile, to which I was very pleased about._

 _"Sir, could I please have a paper?" I asked._

 _He nodded and gave me the paper, trading it for the dollar I had in my hand. Just as he was about to swipe his hand away from me, I saw him shake his head._

 _"What's wrong?" I asked._

 _"You gave me too much money, it only costs a penny. I can't take this." stated the newsboy._

 _"Keep it. You need it more than I do." I smiled._

 _"Thanks. You're nice, nicer than some o' the bags livin' 'round here anyway." he said._

 _"Thank you." I laughed._

 _"I'm Jack Kelly." introduced the newsboy._

 _"I'm Alyssa Montgomery." I replied._

 _"As in Frank Montgomery's daughter?" questioned Jack._

 _"Yes." I nodded._

 _"It was nice meeting you." smiled Jack._

 _And with those final words, Jack walked off. And I stood there shocked._

Everyone had always said newsies were vermin and a disgrace to the city. I hadn't ever met one, not until that day. And from that one meeting, my view on newsies was changed. From then on, I began to see more and more of Jack around the city, and became closer to him everyday. Soon, I met the rest of the Manhattan newsies and became close to them as well.

Everything was fine. My father thought I was with my friends all day, but really I was with the newsies. Everyone was happy. Until something horrible happened. Something that made me have to choose between the two most important things in my life.

 **Thanks everyone for reading the first chapter. If you would like to know what Alyssa looks like there is a link on my profile, Hope you enjoyed this chapter and please follow, favourite and comment. Bye. Xxx.**


	2. Chapter 1

It was a day like any other. I woke up, got dressed and went downstairs to see my father sat down reading yesterday's newspaper. I smiled politely at him, to which he nodded at me as a sign of acknowledgment.

"Father, I'm going to meet Christina at her house." I spoke.

"Have fun, just remember to buy me a paper." responded my father.

I nodded, before walking out the door. My father said the exact same thing to me every morning, although I had no reason to complain; I was friends with the newsies, and if my father saw me hanging out with them, all I had to say was I was getting him a paper.

As I walked deeper and deeper into Manhattan, I began to see Jack and the other Manhattan newsies stood near the square. Smiling, I began running towards them, as soon as I reached them, they all waved at me and smiled.

"Alright, Lys?" greeted Jack.

"Hi. Can I have your first paper today?" I asked.

"Your fadder wantin' one again?" questioned Jack.

"Like always." I smiled, as Jack chuckled.

Just as the sentence left my mouth, the Delancey brothers came walking towards us. Ever since the first time Jack brought me with him to get papers, I had hated the Delancey brothers. They were really creepy. That was probably the reason why they were behind bars giving out papers to newsies, instead of selling them to innocent people on the streets.

"Dear me! What is that unpleasant aroma. I fear the sewer may have backed up during the night." said Race.

"Nah, too rotten to be the sewers." joined in Boots.

"It must be the Delancey brudders." finished Crutchy.

"Hiya boys." spoke Race, as I giggled next to him.

"See, you still got the stupid little girl wid ya'." commented Oscar, as he looked at me in disgust. "In the back you lousy little shrimp."

Oscar then proceeded to push me to the ground as I looked at him in shock. He had the nerve to do that to a girl. It's absolutely disgusting. Jack came over and helped me up off the ground as I smiled at him in thanks.

"It's not good to do that. Not healthy." said Race.

"You shouldn't call people lousy little shrimps, Oscar, unless you're referring to the family resemblance in your brudda here." tormented Jack.

"5-1 that Cowboy skunks 'em. Who's betting?" asked Race.

"That's right. It's an insult. So's this." mocks Jack.

Within a second, Jack knocked Morris' hat off his head, and ran away with it. The Delanceys chased after him, running round every part of the square, as the newsies and I cheered Jack on. Suddenly, Jack bumped into a boy who I'd never seen round that part of Manhattan before.

"What do you think you're doing?" the boy asked Jack, clearly frustrated.

"Runnin'!" shouted Jack, as he began running off again.

I saw the boy roll his eyes and push the younger boy that was with him in front, as they made their way towards the gates where the newsies collect their papers.  
"Sorry about him." I called, as I ran past them to catch up to the newsies.

I turned the corner to see Oscar tackle Jack to the ground, but Jack wasn't fazed, as he swung his legs behind him, and kicked both the brothers. A second later, everyone was in a circle surrounding Jack, Oscar and Morris, as they fight each other. Oscar went to punch Jack, but fortunately he dodged it and grabed Morris' arm putting him between the both of them, as Oscar went to punch Jack again. Instead, he punched Morris in the face, and Jack took this as an opportunity to throw them into the crowd. As Jack proceeded to climb up the gate, we all cheered louder than we were before, praising Jack on his defeat of the Delancey brothers. The whistle then blowed, signalling the gates were opening, as Jack paid no attention and still stood on them.

"These is for the newsies!" announced a red haired World employee, holding a stack of newspapers.

Everyone started lining up to get the papers, as I stood next to Jack who was at the front of the line. Everyone was still congratulating Jack on his defeat of the Delancey brothers.

"'Lys, you coming with me to the races today? Could really use someone like you there , it's meant to be a tough set o' races." asked Race.

"Sorry Race, I'm going with Jack today. I'll go with tomorrow though." I smiled.

"Yeah, yeah, I understand, you wanna learn from the best and Jack's the best." nodded Race.

Race was one of my best friends in the group, besides Jack. When everyone else was weary about me being the daughter of the richest man in New York, Race treated me like we had been friends for ages, since then we sometimes went to the races together and it proved I was pretty good at picking the horses.

"See you tomorrow, Cowboy." sneered Morris, as he walked past.

"You're as good as dead, Cowboy." 'threatened' Oscar, walking behind him.

I looked up at Jack to see him merely chuckling at them, and rolling his eyes mockingly It was amazing sometimes how brave Jack was. He'd do anything for anyone, it was almost inspiring.  
Jack walked up to the counter with an amused smile on his face. I could already tell he was ready to annoy Mr Wisel, the person who gave out the papers to newsies.

"Oh, Mr Weasel." sang Jack mockingly.

Jack started banging on the counter and ringing the bell continuously, in hopes of annoying Mr Wisel more.

"Alright, alright! Hold your horses! I'm coming, I'm coming." shouted Mr Wisel, trying to get Jack to stop ringing the bell.

"So, didja miss me Weasel? Huh, did you miss me?" taunted Jack, knowing that Mr Wisel couldn't do anything about it.

I went to sit down on the steps, as I watched the scene in front of me. It was always quite fun to see Jack torment Mr Wisel. Nobody liked him anyway.

"I told ya' a million times the name's Wisel. Mr Wisel to you. How many?" asked Mr Wisel, clearly fed up of Jack already.

"Don't rush me. I'm persuing the merchnadise, Mr _Weasel_." mocked Jack, purposefully carrying along the 'weasel', as he continued tp read the headlines. "The usual."

"100 papes for the wise guy." ordered Mr Wisel. "Next!"

"Morning your honour! Do me favour, spot me 50 papes." spoke Race, as he lit his cigar. "I got a hot tip into the fourth, you won't waste your money."

"It's a sure thing?" questioned mr Wisel.

"Yeah. Not like last time." nodded Race.

"50 papes! Next!" called Mr Wisel.

Race came and sat next to me, before looking through the paper, as was Jack.

"See anything good this morning?" asked Race

"Not yet." answered Jack.

"Can I have a look?" I asked.

"Sure, go ahead." nodded Race, as he handed me the paper.

The two boys we saw before when Jack was fighting Oscar and Morris, were next in line, but the younger one came nervously walking towards us to wait for who I assumed was his brother.

"You wanna sit down?" asked Jack to the young boy, who nodded eagerly.

"20 papes. please." I heard the older boy ask Mr Wisel."Thanks."

I smiled, happy to know that some people were polite around here. I loved the boys, but they never said 'please' or 'thank you' to Mr Wisel. It's just general politeness, even if it was him.

I carried on reading the paper, until I came upon a very strange one, which would catch anyone's eye.

"'Baby born with two heads.'"I read.

"Must be from Brooklyn." chuckled Race, as I laughed beside him.

I never understood, but whenever anybody insulted Brooklyn you had to laugh. It was probably because it was the toughest part of New York, and insulting it didn't happen very often.

"Hey, you got your papes, now beat it!" demmanded Mr Wisel to the new boy.

I looked to see the new boy, counting the papers that had previously been given to him.

"I paid for twenty. I only got nineteen." pointed out the boy.

"Are you accusing me of lying, kid?" questioned Mr Wisel.

"No. I just want my paper." argued the boy.

Not many people argued with Mr Wisel, mainly because he was always moody, but if you did it was always a brave move, especially for a new kid.

"He said beat it!" shouted Morris.

A moment later Jack walked up to the counter and started to count the new boys papers. I got up and stood beside Jack ready to stop him if he tried to cause an argument.

"No, it's nineteen. It's nineteen, but don't worry about it." spoke Jack.

"It's an honest mistake." I ntervened, in hopes of calming someone down, but it didn't seem to work.

"Exactly." agreed Jack. "Morris here can't count twenty with his shoes on. Lys, Race, will ya' spot me two bits?"

I handed him one, while Race flicked another one over to him, which Jack swiftly caught. It was good to know that Jack wasn't trying to cause an argument like he usually does with the Delancey brothers.

"Another 50 for my friend." demmanded Jack, as he slapped the new boy on the back.

"I don't want another 50." argued the boy.

"Sure you do. Every newsie wants more papes." said Jack, whilst handing him the papers.

"Or so they say." I spoke up.

"And what they say is true."said Race, coming to stand next to me.

We all began to walk away from the counter, heading towards the dirty, old streets of New York, ready to start a new day of selling.

"I don't. I don't want your papes. I don't take charity from anyone. I don't know you. I don't care to. Here are your papes." ranted the new boy, trying to hand Jack the papers.

"Cowboy. They call him Cowboy." jeared in the younger boy.

"Yeah, I'm called that an' a lot o' other things, including Jack Kelly, which is what me mudder called me." nodded Jack.

"And I'm Alyssa." I introduced, while I got the chance to. "So, what do they call you, kid?"

"Les. And this is my brother David. He's older." smiled the younger boy.

"No kidding." spoke Jack, while I chuckled. "So, how old are you, Les?"

"Near ten." answered Les confidently.

"Cute." I commented.

"Near ten? Well, that's no good. If anyone asks you're seven." ordered Jack. "You see younger sells more papes and if we're gonna be partners, we wanna be the best."

"Wait, who said anything about being partners?" protested David.

"Yeah, who said anything about being partners?" I chimed in, wondering what I was going to do for the rest of that day.

David looked at me strangely, before turning back to Jack to find out an answer to his question.

"Well, you owe me two bits, right? Well, I'll consider that an investment. We'll sell together, we split 70-30, plus you get the benefit of observing me, no charge." suggested Jack.

"A-ha." laughed David, obviously thinking it was a joke.

"A-ha." mocked Jack, as I giggled next to him.

"You getting the chance of a lifetime here, Davey."said Crutchy, stepping in. "You learn from Jack, you learn from the best."

Jack turned round to high five and fist bump with some newsies, while we chuckled at Crutchys comment, obviously agreeing with him.

"Well, if he's the best, how come he needs me?" asked David.

"Listen, I don't need you, pal,but I ain't got a cute little brudder like Les here to front for me." argued Jack. "With this kid's puss and my god given talent, we could move a thousand papes a week. So what do you say Les? You wanna sell papes with me?"

"Yeah!" cheered Les, as I giggled.

"So, does Jack have a deal?" I asked.

"Wait, it's gotta be at least 50-50." said David.

"60-40, I forget the whole thing."suggested Jack, as I nodded in agreement.

I heard all the other newsies mumrmur in agreement, as David held out his hand for Jack to shake. Agreeing, Jack spat in his hand and held it out to David, who reluctantely pulled away.

"What'sa matta?" asked Jack.

"Thats disgusting!" shouted David.

"Thank you, soembody who understands that that isn't how you behave in normal society." I spoke.

"Shut up, rich girl." joked Jack, as I giggled.

At that point, the rest of the newsies had collected their papers and were going out onto the streets to sell them.

"The name of the game is volume, Dave." said Jack. "You only took twenty papes, why?"

"Bad headline." stated David.

"See, that's the first thing you gotta learn." informed Jack. "Headlines don't sell papes."

"Newsies sell papes." I joined in with the newsies famous quote.

"You know we're what holds this town together." said Jack. "Without newsies nobody knows nothin'."

At that moment, a pretty girl with brown hair walked past, and the newsies all took off their hats, a few of them complimenting her, as she blushed and walked away.

"Boys." I murmured, rolling my eyes.

"Baby born with three heads!" I heard Specs shout, as the other newsies followed suit.

"What was that you said just then, Lys?" asked Race.

"Oh, just boys. As soon as a pretty girl walks past, it's as if you're in a trance or something." I explained.

"That's 'cos there's no way any of us are ever gonna get her, so we may as well say something, just for the sake of saying it. It's like if you weren't friends with us, you would probably just be another pretty girl on the street that we shouted things at." said Race.

"Ah, I get it."I nodded, turning around. "Wait, where'd Jack go?"

"I think he went with the new kid, David or whatever he's called. So. it looks like you _are_ selling wid me today." smiled Race. " Now, let's head down to the races."

"Okay." I said, before grabbing a paper off him."'Brooklyn baby born with three heads!'"

Race chuckled, before following me in shouting out newspaper headlines, as we walked down the road.

Hurray! For anotther chapter, that was not posted soon enough. I really need to post more often, even if it is only the second chpater.

Thanks to everyone who reviewed, favourited and followed my story. It means so much.

Also, I am English, so it you see anything that doesn't look American, please let me know.

Bye for now! Xxx.


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